Luxury Vacation Home Rentals on Anna Maria Island

Golden hour on Anna Maria Island. In the foreground are beautiful homes, while the ocean and sunset can be seen in the distance. The homes all have a lush, tropical feel - perfect for your next Anna Maria Island luxury vacation!

Discover our Anna Maria Island vacation rentals with private pools, perfect for relaxing getaways with family, friends, or pets. From Anna Maria to Holmes Beach and Bradenton Beach, our homes offer privacy, comfort, and easy access to the island’s best beaches, shops, and restaurants.

Our local team is here to ensure a seamless stay, offering personalized support and insider tips to make your vacation unforgettable. Whether you’re bringing your pup  or planning a family retreat, you’ll find the ideal home for your island escape.

Our 'She's Always Right' Anna Maria Island luxury vacation rental, a soft blue house with white trim and coral-colored doors. This property, along with many others, is pet friendly! There's no need to leave your furry friend at home. They deserve a pet vacation!

Browse our collection of pet-friendly vacation rentals on Anna Maria Island and discover the perfect beach home. Enjoy prime locations and easy access to the island’s top beaches, dining, and attractions.


Vacation rental with a beautiful private pool, located at our Sea La Vie Beach House on the North End of Anna Maria Island. Close to everything, from Pine Avenue’s shops, Bayfront Park, and Gulf beaches, this house has it all.

View our selection of vacation rentals with private pools on Anna Maria Island. Enjoy a refreshing dip any time of day, spacious outdoor living areas, and the perfect blend of relaxation and island charm.


Aerial view of our AcquaLuxe property, and the surrounding area, at sunset. This waterfront luxury vacation rental on Anna Maria Island is one of many offered by Once Upon a Beach, and boasts a heated saltwater pool, private dock, chef’s kitchen, and top-tier amenities for an unforgettable coastal retreat.

Explore the collection of waterfront vacation rentals on Anna Maria Island and find your perfect beach getaway. Wake up to breathtaking views, unwind in style, and experience the best of island living.


Properties Available 38 properties available
Welcome to Cozy Cabana West!On Anna Maria Island (Holmes Beach, Florida)Managed by Once Upon A Beach Vacation Rentals, a locally owned and operated boutique vacation rental agency.Where slow mornings and quiet evenings meet the rhythm of island life.Just a short stroll from Holmes Beach, this thoughtfully designed bungalow invites guests to rest, r
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Cozy Cabana West
Cozy Cabana West
Holmes Beach Pet Friendly
$275.00 - $700.00 / per night
Bedrooms 2 bedrooms
Bathrooms 2 baths
Guests 6 guests
Rating 5 (3)
Welcome to Island Girl West!On Anna Maria Island (Holmes Beach, FL)Managed by Once Upon A Beach Vacation Rentals*This listing is for ONE unit: Island Girl West*Step inside Island Girl West, where natural textures, sunlight, and soft coastal hues set the tone for your stay. The open layout invites easy flow between kitchen, dining, and living spaces
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Island Girl West
Island Girl West
Holmes Beach
$205.00 - $490.00 / per night
Bedrooms 2 bedrooms
Bathrooms 2 baths
Guests 5 guests
Rating 5 (3)
Welcome to Family Tides!On Anna Maria Island (Bradenton Beach, FL)Managed by Once Upon A Beach Vacation Rentals*This listing is for BOTH units; Family Tides A & Family Tides B*Where gathering comes naturally and every generation finds its place in the sun.Just steps from the Gulf of Mexico in Bradenton Beach, this dual-home property offers
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Family Tides
Family Tides
Bradenton Beach
$450.00 - $1,700.00 / per night
Bedrooms 6 bedrooms
Bathrooms 4 baths
Guests 16 guests
Rating 4.8 (9)
Welcome to Mariner's Crossing!On Anna Maria Island (Bradenton Beach, FL)Managed by Once Upon A Beach Vacation Rentals, a locally owned and operated boutique vacation rental agency.The SpaceSet between the Gulf of Mexico and the Intracoastal Waterway, Mariner’s Crossing offers balance — connection and privacy, activity and calm. With
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Mariner's Crossing
Mariner's Crossing
Bradenton Beach
$800.00 - $3,500.00 / per night
Bedrooms 8 bedrooms
Bathrooms 7 baths
Guests 18 guests
Rating 4.9 (12)
Welcome to Sea La Vie Beach House!On Anna Maria Island (Anna Maria, FL)Managed by Once Upon A Beach Vacation Rentals, a locally owned and operated boutique vacation rental agency.The SpaceWhere connection meets calm, Sea La Vie Beach House brings family, friends, and loved ones together in a space designed for comfort, laughter, and easy island liv
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Sea La Vie Beach House
Sea La Vie Beach House
Anna Maria
$600.00 - $1,750.00 / per night
Bedrooms 4 bedrooms
Bathrooms 4 baths
Guests 8 guests
Rating 5 (9)
Welcome to Catching Waves!On Anna Maria Island (Holmes Beach, Florida)Managed by Once Upon A Beach Vacation Rentals, a locally owned and operated boutique vacation rental agency.Experience Catching Waves — where laid-back island living meets everyday adventure. Just a short stroll to the white-sand beaches of Holmes Beach, this ground-level h
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Catching Waves
Catching Waves
Holmes Beach Pet Friendly
$225.00 - $650.00 / per night
Bedrooms 2 bedrooms
Bathrooms 2 baths
Guests 6 guests
Rating 5 (3)
Welcome to Family Tides – Unit BOn Anna Maria Island (Bradenton Beach, FL)Managed by Once Upon A Beach Vacation Rentals*This listing is for ONE unit; Family Tides B (Top Unit)*Set above its sister unit in this beautiful duplex, this light-filled home offers space for connection and comfort, with access to shared outdoor amenities designed for
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Family Tides - B
Family Tides - B
Bradenton Beach
$280.00 - $920.00 / per night
Bedrooms 3 bedrooms
Bathrooms 2 baths
Guests 8 guests
Rating 4 (1)
Welcome to La Buena Vida!On Anna Maria Island (Anna Maria, FL)Managed by Once Upon A Beach Vacation Rentals, a locally owned and operated boutique vacation rental agency.The SpaceMornings begin with sunlight dancing across the canal and coffee enjoyed on the screened porch. Days unfold between the pool, the dock, and the nearby beach—each mom
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La Buena Vida
La Buena Vida
Anna Maria Pet Friendly
$380.00 - $890.00 / per night
Bedrooms 3 bedrooms
Bathrooms 3 baths
Guests 8 guests
Rating 4.8 (5)
Welcome to Coconut Lagoon!On Anna Maria Island (Anna Maria, FL)Managed by Once Upon A Beach Vacation Rentals, a locally owned and operated boutique vacation rental agency.The SpaceStep into Coconut Lagoon, where generations of island charm meet easy, family-focused living. Nestled along the beloved Magnolia Avenue—lined with palms, bike
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Coconut Lagoon
Coconut Lagoon
Anna Maria Pet Friendly
$350.00 - $850.00 / per night
Bedrooms 3 bedrooms
Bathrooms 2 baths
Guests 6 guests
Rating 4.9 (16)
Welcome to Ocean Sunrise!On Anna Maria Island (Bradenton Beach, FL)Managed by Once Upon A Beach Vacation RentalsThe SpaceSet directly on the Bay in Bradenton Beach, Ocean Sunrise offers 4,793 square feet of bright, inviting living. The design balances elegance and ease—sun-filled rooms, expansive gathering spaces, and a backyard where the lin
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Ocean Sunrise
Ocean Sunrise
Bradenton Beach
$700.00 - $2,500.00 / per night
Bedrooms 6 bedrooms
Bathrooms 4 baths
Guests 20 guests
Rating 5 (1)
Welcome to Sea La Vie!On Anna Maria Island (Anna Maria, FL)Managed by Once Upon A Beach Vacation Rentals, a locally owned and operated boutique vacation rental agency.The SpaceWhere light dances across the water and modern design meets island ease, Sea La Vie invites you to experience the beauty of Anna Maria Island from a space that feels both lux
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Sea La Vie
Sea La Vie
Anna Maria
$510.00 - $1,600.00 / per night
Bedrooms 3 bedrooms
Bathrooms 3 baths
Guests 8 guests
Rating 5 (3)
Welcome to Island Girl East!On Anna Maria Island (Holmes Beach, FL)Managed by Once Upon A Beach Vacation Rentals*This listing is for ONE unit: Island Girl East*Discover Island Girl East, a bright coastal retreat just five houses from the beach. Here, mornings begin with the sound of swaying palms, and afternoons drift between the pool and the sea.
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Island Girl East
Island Girl East
Holmes Beach
$205.00 - $490.00 / per night
Bedrooms 2 bedrooms
Bathrooms 2 baths
Guests 5 guests
Rating 5 (1)

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When is the best time to visit Anna Maria Island?

Anna Maria Island is beautiful any time of year, but different seasons are best for different activities. Spring and fall both have warm temperatures and fewer crowds, and are perfect for a more relaxed vacation spent enjoying the outdoors and checking out local attractions. Summer is the hottest and busiest time of year. If you’re looking for exciting summer energy, summer is your best bet. Winter in Anna Maria Island has cooler temperatures and the lowest prices.

Are dogs allowed on the beaches in Anna Maria Island?

Most of the beaches on Anna Maria Island do not allow dogs, so it’s important to check the regulations before bringing your pup. But even if you can’t bring your four-legged family member to one of the main beaches, there are plenty of alternatives, like Palma Sola Causeway Park & Bayfront Park. View Pet Friendly Rentals in Anna Maria Island.

What are the best beaches on Anna Maria Island?

Every beach on the island is fantastic! We love Bean Point, on the northern tip of the island, for its views, wildlife viewing, and spectacular shelling. Bradenton Beach is great for anyone looking for a mix of relaxation and activities, with easy access to biking trails and restaurants. And Holmes Beach is lovely for anyone who wants to swim in clear waters or relax in the sugar-soft sands the island is famous for. Rentals within walking distance to the beach

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